Isoamylamine → n[3(s)-Benzyloxycarbonylamino-2(r)-hydroxy-4-phenylbutyl]n-isoamylamine

HRID 725902Notes

Reaction equation

HRID 725902 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:13]1[O:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH2:28])[CH2:24][CH:25]([CH3:27])[CH3:26]>C(O)(C)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:13]([OH:15])[CH2:14][NH:28][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Product 1

HCID 10430124n[3(s)-Benzyloxycarbonylamino-2(r)-hydroxy-4-phenylbutyl]n-isoamylamineYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of N-benzyloxycarbonyl 3(S)-amino-1,2-(S)-epoxy-4-phenylbutane (30.1 g, 0.10 mol) and 165 mL of isoamylamine in 150 mL of isopropyl alcohol was heated to reflux for 2.5 hours. The solution was cooled to room temperature, concentrated in vacuo and then recrystallized. The product was isolated by filtration and from ethyl acetate/hexane to afford 31.7 g (81%) of N[3(S)-benzyloxycarbonylamino-2(R)-hydroxy-4-phenylbutyl]N-isoamylamine.

Workup

  1. temperatureto reflux for 2.5 hours
  2. concentrationconcentrated in vacuo
  3. customrecrystallized
  4. customThe product was isolated by filtration and from ethyl acetate/hexane

Sources & evidence

ORD record
ord-cb6e27112590467f85649ddbe83863d9
Source dataset
uspto-grants-1998_01
Patent number
US05708004

Reaction notes

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